Izenamide A

Details

• Internal ID: 9eb75ce4-a0cc-49f5-a423-a2740fb384d3
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides
• IUPAC Name: methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S,3S)-2-[[(3S,4S)-3-hydroxy-4-[[(2R)-2-[(2S)-2-hydroxy-3-methylbutanoyl]oxy-3-methylbutanoyl]amino]-6-methylheptanoyl]amino]-3-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• SMILES (Canonical): CCC(C)C(C(=O)NC(C)C(=O)N(C)C(CC1=CC=CC=C1)C(=O)N2CCCC2C(=O)OC)NC(=O)CC(C(CC(C)C)NC(=O)C(C(C)C)OC(=O)C(C(C)C)O)O
• SMILES (Isomeric): CC[C@H](C)[C@@H](C(=O)N[C@@H](C)C(=O)N(C)[C@H](CC1=CC=CC=C1)C(=O)N2CCC[C@H]2C(=O)OC)NC(=O)C[C@@H]([C@H](CC(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)O)O
• InChI: InChI=1S/C43H69N5O11/c1-12-27(8)35(46-34(50)23-33(49)30(21-24(2)3)45-39(53)37(26(6)7)59-43(57)36(51)25(4)5)38(52)44-28(9)40(54)47(10)32(22-29-17-14-13-15-18-29)41(55)48-20-16-19-31(48)42(56)58-11/h13-15,17-18,24-28,30-33,35-37,49,51H,12,16,19-23H2,1-11H3,(H,44,52)(H,45,53)(H,46,50)/t27-,28-,30-,31-,32+,33-,35-,36-,37+/m0/s1
• InChI Key: LTKVRJFDYIZQCP-ALAILQQQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₉N₅O₁₁
• Molecular Weight: 832.00 g/mol
• Exact Mass: 831.49935803 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 22

Synonyms

• CHEMBL4169189
• DTXSID501046511
• BDBM50361188

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5252	52.52%
Caco-2	-	0.8639	86.39%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6909	69.09%
OATP2B1 inhibitior	-	0.7131	71.31%
OATP1B1 inhibitior	+	0.8505	85.05%
OATP1B3 inhibitior	+	0.8986	89.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8321	83.21%
P-glycoprotein inhibitior	+	0.7490	74.90%
P-glycoprotein substrate	+	0.8615	86.15%
CYP3A4 substrate	+	0.7319	73.19%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8175	81.75%
CYP3A4 inhibition	-	0.6464	64.64%
CYP2C9 inhibition	-	0.8267	82.67%
CYP2C19 inhibition	-	0.7977	79.77%
CYP2D6 inhibition	-	0.9097	90.97%
CYP1A2 inhibition	-	0.8925	89.25%
CYP2C8 inhibition	+	0.6351	63.51%
CYP inhibitory promiscuity	-	0.8886	88.86%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6784	67.84%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9091	90.91%
Skin irritation	-	0.8027	80.27%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6654	66.54%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.8958	89.58%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4668	46.68%
Acute Oral Toxicity (c)	III	0.6638	66.38%
Estrogen receptor binding	+	0.8429	84.29%
Androgen receptor binding	+	0.7147	71.47%
Thyroid receptor binding	+	0.6051	60.51%
Glucocorticoid receptor binding	+	0.7600	76.00%
Aromatase binding	+	0.5869	58.69%
PPAR gamma	+	0.7828	78.28%
Honey bee toxicity	-	0.7372	73.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8972	89.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2581	P07339	Cathepsin D	380 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.32%	90.17%
CHEMBL3837	P07711	Cathepsin L	99.31%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.32%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	95.75%	89.63%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	95.72%	98.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.88%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.29%	93.56%
CHEMBL2514	O95665	Neurotensin receptor 2	91.28%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	91.20%	91.19%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	90.98%	97.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.56%	99.17%
CHEMBL4072	P07858	Cathepsin B	87.93%	93.67%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.37%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.33%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	86.86%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.37%	96.00%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	86.20%	98.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.74%	100.00%
CHEMBL2535	P11166	Glucose transporter	85.46%	98.75%
CHEMBL3202	P48147	Prolyl endopeptidase	85.46%	90.65%
CHEMBL204	P00734	Thrombin	85.35%	96.01%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.85%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.74%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.67%	97.09%
CHEMBL5028	O14672	ADAM10	83.27%	97.50%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.39%	94.66%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 132505928
• LOTUS: LTS0225136
• wikiData: Q104203268